96887-44-4Relevant academic research and scientific papers
Concise synthesis of two trisaccharides related to the saponin isolated from Centratherum anthelminticum
Mandal, Santanu,Mukhopadhyay, Balaram
, p. 11363 - 11370 (2007)
Chemical synthesis of two trisaccharides related to the saponin isolated from Centratherum anthelminticum is reported. Stereoselective, high-yielding glycosylation strategies were developed using H2SO4 immobilized on silica for activ
Organoboron-Promoted Regioselective Glycosylations in the Synthesis of a Saponin-Derived Pentasaccharide from Spergularia ramosa
Mancini, Ross S.,McClary, Corey A.,Anthonipillai, Stefi,Taylor, Mark S.
, p. 8501 - 8510 (2015/09/15)
Organoboron-mediated regioselective glycosylations were employed as key steps in the total synthesis of a branched pentasaccharide from a saponin natural product. The ability to use organoboron activation to differentiate OH groups in an unprotected glycosyl acceptor, followed by substrate-controlled reactions of the obtained disaccharide, enabled a streamlining of the synthesis relative to a protective group-based approach. This study revealed a matching/mismatching effect of the relative configuration of donor and acceptor on the efficiency of a regioselective glycosylation reaction, a problem that was solved through the development of a novel boronic acid-amine copromoter system for glycosyl acceptor activation.
